Good Old Boat Magazine had an excellent article on building a tabernacle, about a year or two ago... That issue is at my office and I'm stuck at home with a broken ankle. But you should be able to acquire that article and see how simple it is to use.
But then putting some young teenagers out at the end of the boom to list your boat is a fun idea for them...

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Telstar 28
New England

You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.

—Cpt. Mal Reynolds, Serenity (edited)

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Ok, I now understand a little better the gravity of the project and can see that it would not really be be feasible when looking at it from all aspects. This was the point of my questions. It was definitely a good exercise of the mind though, which was also the point of sitting around and discussing it. Friends and I have debated this subject for quite some time now and this thread has sparked some new points of view. A Tartan 27 has 38' of bridge clearance stock. that means I could pass under the bridge 50% of the time. May just have to watch the tide charts very closely until I finally move to a different marina. Thank you all for your thoughts. Alan

We previously moored our boat behind a large bridge (clearance was not an issue) but the tide-driven currents were just about as big an obstacle to passage as low clearance.. We had to time our arrivals/departures around Mother Nature's immovable schedule and it wasn't really too bad.

Now that we're elsewhere it's much better, of course, but it was a rare day that we couldn't get out at some point...

I do think, though, that trying to find a boat that meets your requirements in stock form will be a better approach.

Alan, what you want to do certainly can work. And since you are not concerned with losing the entire resale value of the boat (and an "oddball" boat may go unsold for a very long time even at a low price) we can dismiss that issue.

But are you at all concerned with the performance and balance of the boat? It is very easy to ruin the balance of a boat, and a lot of math goes into putting the various centers of effort and rotation and all into "good" positions versus mediocre ones. When you say:
"Step 1) Make a mark 1' 6" down from the top of the mast....
3) Have new rigging made for the boat exactly 1' 6" shorter than the rigging that came off it."
I have to think that you do not have any grasp on how complex the 3-dimensional geometry of a sailboat hull or rig actually is. Remember, the "rigging" includes forestay and backstay and since they run at angles to the mast--they will NOT simply be the same distance shorter that the mast is.
Similarly, depending on the cut of your sails, taking 18" off the bottom may not be the best way to recut them. You'd want to run some numbers--or have a loft run them--to see if recutting the sails or making new ones would be more effective than just pretending there was an 18 reef in the sails.
Many boats are built with optional tall/short rigs/keels and when they make those changes, the builders usually don't just lop off a couple of feet.
If you don't mind taking a good boat and, basically, gambling on turning it into a "Dodge Dart", a vessel that sails but who knows how well or poorly...by all means.
But I'd really urge talking to some riggers, some sailmakers, and the factory and getting some insight into just what troubles you may get into by just lopping 18" off the mast.
Yes, it can be done. But the more you look into the details, the more it MAY seem that it would be cheaper, faster, simpler, to just buy a short mast version of a production boat.

I converted my O'Day Mariner (19'6" LOA) from a deck stepped mast to a keel stepped mast which in effect shortened my 24' mast by about 2'6". I didn't relocate anything, just shortened everything up. I can't tell anything really different handling except that -maybe- it heels a little less, but not much.

The Mariner is a daysailer so it may not be a good indicator of your boats performance, but if money isn't the issue I say go for it and see how it does. Worst case you have to add the length back. I don't see this as a serious safety issue. I do think it's good advice to talk to the manufacturer.

You said you like to customize-me, too. I can't leave anything stock. Around here we call it kit bashing. Just finished putting lower gears and lockers in my 4X4 Toyota. I don't think my Yamaha VMax has any stock parts left on it !!!

Keep your lovely marina two options
A Do what you plan yes it will affect the light airs sailing and it will improve stability but it will be a lot of bother and drop the value of your boat. I am thinking of doing this so I can take my small Galion 22 across oceans but I will be cutting my mast down a lot more and adding a yawl mizzen.

or

B Get a 5 gallon plastic jerry can drill a hole in the bottom fit a rubber cork with a peice of string, fit a thin plastic hose to the top attach the whole thing to a halyard and haul it to the top of the mast. Attach the hose to a 12 volt water pump and pump sea water up into the jerry can that weight being so far up the mast will cause the boat to list now motor or sail under the bridge using the jib or motor. Pull the string to remove the cork or you could just detach the hose from the pump and back siphon the water away. Now lower the empty jerry can stow and sail on. This solves your problem witout any of the disadvantages or hassle of plan A

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